A recyclable self-assembled composite catalyst consisting of Fe3O4-rose bengal-layered double hydroxides for highly efficient visible light photocatalysis in water

Article abstract of DOI:10.1039/c8cc08130a

The first case of a highly efficient layered double hydroxide (LDH) supported organic visible light photocatalyst is reported and it can catalyze various organic transformations with high efficiency in water under visible light irradiation.

Full text of DOI:10.1039/c8cc08130a

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A recyclable self-assembled composite catalyst
consisting of Fe O -rose bengal-layered double
hydroxides for highly efficient visible light
3
4
Cite this: Chem. Commun., 2018,
4, 13587
5
Received 10th October 2018,
Accepted 8th November 2018
photocatalysis in water†
Yuxing Huang, ‡ Zhuo Xin, ‡ Wenlong Yao, Qi Hu, Zhuohua Li, Liuqing Xiao,
DOI: 10.1039/c8cc08130a
Bo Yang
and Junmin Zhang
*
rsc.li/chemcomm
8
,9
The first case of a highly efficient layered double hydroxide (LDH) low cost. However, studies on LDH supported visible light
1
0
supported organic visible light photocatalyst is reported and it can photocatalysts are few. To the best of our knowledge, there is
catalyze various organic transformations with high efficiency in no report on LDH supported organic photoredox catalysts.
water under visible light irradiation.
Interestingly, LDHs are often employed as low-cost adsorbents
for removing anionic organic dyes from the environment
1
1
Chemical transformations driven by visible light at ambient through electrostatic interaction. Therefore, we envisaged that
temperature are highly desirable based on the concept of green rose bengal, the aforementioned anionic organic dye visible light
and sustainable chemistry. Therefore, visible light photo- photocatalyst, could be immobilized on LDHs to solve the catalyst
catalysis has attracted significant attention from chemists recycling problem.
1
and considerable progress has been made in this field. Many
Herein, we reported the first case of a LDH supported
reports have discussed using precious transition metal based organic photoredox catalyst and its application in various
visible light photocatalysts, such as polypyridyl ruthenium and chemical transformations. This composite catalyst, designated
3 4
iridium photoredox catalysts, for the construction of challenging as Fe O -RB/LDH, can be easily obtained with the help of an
2
covalent bonds under mild conditions. On the other hand, ultrasonic technique in the environmentally benign medium,
organic photoredox catalysts have been studied intensively as a water. The stable self-assembly is achieved via electrostatic
sustainable replacement of their precious metal based counter- interaction among the anionic rose bengal (RB) dye, negatively
parts due to their high cost and scarcity. Among them, several charged magnetite nanoparticles, and positively charged LDHs.
organic dye based visible light photocatalysts have been success- Moreover, Fe O -RB/LDH demonstrated high catalytic activity
3
4
fully applied in various chemical transformations, such as rose in several different types of photocatalytic reactions in water,
3
bengal, eosin Y, rhodamine dyes, etc. Nonetheless, both transi- and can be easily recovered using a magnet with good efficiency
tion metal and organic dye based photocatalysts face the same in recycling experiments.
problem in catalyst recycling for reuse due to their homogeneous
MgAl–LDH was chosen as the solid support purposefully,
properties in the reaction system. To overcome this obstacle, one as a theoretical study has shown that MgAl–LDH is UV-light
needs to find proper carrier materials to immobilize these responsive and therefore will not interfere the visible light
4
12
photocatalysts and thus achieve the recyclability. Silicas,
photocatalysis in this study. The preparation of Fe O -RB/
3 4
5
6
7
polymers, metal–organic frameworks (MOFs), and graphene
LDH is illustrated in Scheme S1 (ESI†). Basically, MgAl–LDH
have already been employed in the immobilization of homo- powder was firstly well dispersed in water after an ultrasonic
genous photocatalysts. process. The resulting suspension was then mixed with a citrate
Layered double hydroxides (LDHs) represent a big family of acid capped Fe NP (negatively charged) suspension under
3 4
O
two dimensional layered anionic clay nano-materials, which ultrasonication. After that, a solution of rose bengal in water
have been employed as supports for various catalysts due to was added to the mixture and the three components were
their high positive layer charge density, relatively large surface further mixed by ultrasonication. In the end, the three compo-
area, flexible composition, straightforward preparation and nent self-assembled composite was collected using a magnet
and dried in an oven to afford Fe O -RB/LDH.
3
4
It should be pointed out that the sequence of mixing MgAl–
LDH with Fe NPs before rose bengal is important. If the
MgAl–LDH is mixed with rose bengal prior to Fe NPs, then
the Fe NPs cannot be adsorbed by the MgAl–LDH and rose
College of Chemistry and Environmental Engineering, Shenzhen University,
Shenzhen, 518060, P. R. China. E-mail: zhangjm@szu.edu.cn
3 4
O
3 4
O
†
‡
Electronic supplementary information (ESI) available. See DOI: 10.1039/c8cc08130a
These authors contributed equally to this work.
3 4
O
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bengal composite. Hence, the MgAl–LDH and rose bengal Table 1 Optimization of the reaction conditions for Fe
composite lacks magnetism. This implies that the surface
3
O
4
-RB/LDH
a
catalyzed CDC reactions
charge of the rose bengal adsorbed MgAl–LDH is too negative
to attract the negatively charged Fe O NPs. This is reasonable
3
4
as we only added the Fe O NPs into the system with a mass
3
4
ratio of 0.2 compared to the MgAl–LDH, while the amount of
rose bengal is in excess. Zeta potential measurement results
demonstrated the gradual change of the surface charge of the
material under study. The zeta potential of the MgAl–LDH
suspension in water after ultrasonication is 43.67 mV. After
mixing with the Fe O NPs, the zeta potential reduced to
b
Entry
Solvent
LEDs
Yield (%)
1
2
3
4
5
6
EtOH
DMF
DMSO
DCM
On
On
On
On
On
On
On
Off
On
78
66
53
49
12
91
5
3
4
Toluene
À11.57 mV, indicating the coating of MgAl–LDH with the
H
2
H
2
H
2
H
2
O
O
O
O
c
negatively charged Fe O NPs. The zeta potential of the final
7
3
4
d
8
0
0
Fe
3
O
4
-RB/LDH composite is À22.6 mV, which suggests the
e
9
further adsorption of the anionic rose bengal dye.
a
Reaction conditions: tertiary amine (0.1 mmol), nitromethane
-RB/LDH with different solvents. The catalyst
loading is based on RB. The reaction was performed at room tempera-
ture with 12 W green LEDs for 24 hours. Yield determined by H NMR
with 1,3,5-trimethoxybenzene as an internal standard. In this case, a
The XRD spectra of the samples are collected and further
analyzed (ESI,† Fig. S4A). The diffraction pattern of curve i can
3 4
(1.0 mmol), 4 mol% Fe O
1
3
b
1
be indexed to a cubic spinel phase of Fe
3
O
4
(JCPDS #88-0866).
c
Curve iii shows the XRD pattern characteristic of the MgAl–LDH
d
1
4
free rose bengal disodium salt was used as the catalyst. Without light.
structure with a rhombohedral symmetry (JCPDS #37-0630).
e
Without catalyst.
The diffraction peaks around 351 and 361 in curve ii can be
attributed to the (012) and (311) crystal planes of MgAl–LDH
and Fe
3
O
4
, respectively, which clearly suggests that the Fe
3
O
4
-
on MgAl–LDH, and it was determined by UV-vis spectroscopy
RB/LDH composite contains at least Fe
3 4
O and MgAl–LDH. (ESI,† Table S1). Different solvents were screened and the results
The rose bengal sample shows an unrecognizable diffraction are shown in Table 1. Polar organic solvents, such as EtOH,
pattern in powder XRD (ESI,† Fig. S2) and therefore its exis- DMF, DMSO and DCM, afforded moderate to good yields
tence in the Fe O -RB/LDH composite cannot be confirmed by (Table 1, entries 1–4). The non-polar solvent toluene gave very
3
4
the powder XRD technique. However, the red color of Fe O - low yield (Table 1, entry 5). Interestingly, excellent yield was
3
4
RB/LDH clearly indicates the existence of rose bengal in this obtained with water (Table 1, entry 6). This result provides a new
composite, which is further evidenced by the solid state UV-vis demonstration of a LDH based material as the catalyst in green
1
8
spectra (ESI,† Fig. S4B) and SEM mapping results. The solid aqueous media. We proposed that the citrate acid capped
state UV-vis spectrum of MgAl–LDH shows no absorption in the Fe NPs and rose bengal might form an organic layer on the
visible light region, which corresponds to the aforementioned surface of MgAl–LDH, which attracts the organic substrates from
3 4
O
1
2
3 4
theoretical study result. Both rose bengal and Fe O -RB/LDH the water phase to this organic layer and thus facilitates the
show maximum absorption around 558 nm, which strengthens progress of visible light photocatalysis. The reaction failed in
our confidence in testing the novel Fe O -RB/LDH catalyst for using a free rose bengal disodium salt as the catalyst in water
3
4
visible light photocatalysis. This observation also proves the (Table 1, entry 7). The reaction also failed without light or
existence of rose bengal in the Fe
3
O
4
-RB/LDH.
catalyst (Table 1, entries 8 and 9).
The MgAl–LDH and Fe -RB/LDH samples were analyzed by
3
O
4
We further screened other substrates for this photocatalytic
scanning electron microscopy (SEM) and quantitative energy- CDC reaction under the optimized conditions to demonstrate
dispersive X-ray spectroscopy (EDS). The similar morphology of the broad range of applications of the Fe -RB/LDH. As shown
MgAl–LDH and Fe -RB/LDH shown by SEM suggests that the in Table 2, a series of substituted tetrahydroquinoline deriva-
3 4
O
3 4
O
MgAl–LDH support structure remains intact after several rounds tives were successfully coupled with nitroalkanes to afford the
of ultrasonication process (ESI,† Fig. S3). Furthermore, the SEM desired coupling products in moderate to good yields. The
mapping results show the even distribution of the Fe O NPs and results were comparable to those of our former study and other
3
4
1
6,17
3 4
rose bengal in Fe O -RB/LDH (ESI,† Fig. S5).
literature reports.
The yields for electron rich and electron
With this novel catalyst in hand, we first tested its catalytic deficient N-phenyl rings were quite close, indicating that the
1
5
activity in cross-dehydrogenative coupling (CDC) reactions.
electronic effect is not prominent (Table 2, entries 3a, 3b, 3e–3g).
These kinds of reactions are highly desirable for their capability Nitroethane and nitropropane only afforded 69% and 62% of the
of constructing carbon–carbon bonds directly from two different desired products, respectively, which can be attributed to the
1
6
19
C–H bonds. Moreover, rose bengal based homogeneous and steric effect (Table 2, 3c and 3d).
1
7
heterogeneous catalytic systems have already been reported to
As a fundamental organic transformation, oxidation reactions
efficiently catalyze CDC reactions under visible light irradiation. have been studied extensively. Among them, the sulfoxidation of
N-Phenyl tetrahydroisoquinoline and nitromethane were chosen sulphides attracts great attention due to its vital role in many fields,
20
as substrates for the model reaction in this investigation. The such as the pharmaceutical industry, environmental protection
2
1
22
catalyst loading is based on the amount of rose bengal anchored (wastewater treatment),
and crude oil desulfurization.
1
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Table 2 Fe
Communication
3
a
O
4
-RB/LDH catalyzed CDC reaction of tertiary amines and
Table
4
Fe
3
O
4
-RB/LDH catalyzed anti-Markovnikov radical addition
a
nitroalkanes
reactions of thiols and alkenes
a
Reaction conditions: alkene (0.2 mmol), thiol (0.3 mmol), 5 mol%
3 4
Fe O -RB/LDH. The catalyst loading is based on RB. The reaction was
a
performed at room temperature in 5 mL water for 2 h. A 15 W white LED
lamp was used as the light source. The reaction system was connected
to open air. The yields are isolated yields.
Reaction conditions: tertiary amine (0.1 mmol), nitromethane (1.0 mmol),
mol% Fe -RB/LDH. The catalyst loading is based on RB. The reaction
4
3 4
O
was performed at room temperature in water with 12 W green LEDs (light-
emitting diodes) for 24 hours. The yields are isolated yields.
system with the atmosphere so that further oxidation is not
initiated due to the limited reaction time. In this case, only a
reaction time of 2 hours was taken. However the oxidation reac-
tions shown in Table 3 need 24 hours to 72 hours reaction time to
a
3 4
Table 3 Fe O -RB/LDH catalyzed aerobic oxidation of various sulfides
3 4
achieve satisfactory conversion. However, the effect of Fe O -RB/
LDH cannot be excluded and we are currently investigating the real
mechanism (for the proposed mechanism, see the ESI,† Fig. S10).
We also investigated the recyclability of Fe O -RB/LDH as a
3
4
heterogeneous photocatalyst, and we chose the CDC reaction
of N-phenyl tetrahydroisoquinoline and nitromethane as the
model reaction. The catalyst can be conveniently removed from
the reaction system by using a magnet. The catalyst can be
reused 6 times without a significant loss of the catalytic activity
(see the ESI,† Fig. S9).
In conclusion, by exploiting the electrostatic interaction, we
have successfully developed a facile and efficient protocol for
preparing a novel organic–inorganic composite photocatalyst
a
3 4
Reaction conditions: thioether (0.5 mmol), 2 mol% Fe O -RB/LDH.
The catalyst loading is based on RB. The reaction was performed in
open air at room temperature in 5 mL water, with 15 W CFL (compact (Fe
fluorescent lamp) as the light source. The yields are isolated yields.
3 4
O -RB/LDH) through self-assembly. This new composite
photocatalyst demonstrates excellent photocatalytic activity in
various organic transformations in water under visible light
irradiation, including cross-dehydrogenative coupling reactions,
oxidation reactions and radical addition reactions. The study of
immobilizing other anionic organic photocatalysts together
with chiral catalysts on MgAl–LDH to achieve possible enantio-
selective photocatalysis is currently underway in our labora-
tories and will be reported in due course.
Li and Yao et al. have elegantly demonstrated the ability of rose
bengal and solid-supported rose bengal in highly efficient and
2
3
selective aerobic sulfoxidation under visible light irradiation.
Therefore, we chose this kind of oxidation reaction for further
investigation on the catalytic activity of the Fe -RB/LDH. A
series of thioethers were employed as substrates and the reaction
results are summarized in Table 3. The results are comparable
with those of the former report. The alkylarylthioether substrates
gave excellent yields (Table 3, 5a, 5b, 5d–5g) while diphenyl-
thioether afforded moderate yield (Table 3, entry 5c).
3 4
O
We acknowledge the generous financial support from the
National Natural Science Foundation of China (21402124 and
2
1777106), the Training Foundation for Outstanding Young
Teachers in Higher Education Institutions of Guangdong
YQ2015145), the Project of Featured Innovation in Higher Educa-
(
To demonstrate the wide range of applications of Fe O -RB/
3
4
tion Institutions of Guangdong (2017KTSCX159), the Shenzhen
Science and Technology Foundation (JCYJ20170302143658923),
the PhD Start-up Fund of the Natural Science Foundation of
Guangdong Province (2018A03031061), the Young Scientist Fund of
the Natural Science Foundation of Jiangsu Province (BK20180248)
and the Natural Science Foundation of SZU (827000038). We
gratefully acknowledge the support from the Instrumental Analysis
Center of Shenzhen University (Xili Campus).
LDH in photocatalysis, we employed it for the selective synthesis
of sulfoxides from alkenes and thiols. Interestingly, instead of
2
4
obtaining sulfoxides as Wang et al. reported, in our case the
products are actually thioethers – anti-Markovnikov thiyl radical
addition products of alkenes (Table 4), similar to the results of
2
5
26
Wang and Yoon. In their reports, a thiyl radical is supposed
to be the vital intermediate for the anti-Markovnikov addition
reaction. Indeed, the reaction failed in our study since the 4-tert-
butylcatechol (TBC) radical inhibitor was not removed from the
alkenes. The results of not obtaining sulfoxide products could be
attributed to the insufficient oxygen in our set-up compared to
Conflicts of interest
2
4
that of Wang et al. as we used a needle to connect the reaction There are no conflicts to declare.
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